text: Like first-generation Glycoazodyes, second-generation Glycoazodyes are synthesized using a glucose, galactose, or lactose sugar group. The point of the ether bond is controlled by selectively protecting alcohol groups on the sugar, or by choosing an azo dye with a different alcohol group position. An unprotected alcohol group of either the sugar or the dye is reacted with an n-carbon, terminal dibromoalkane in a solution of potassium hydroxide and 18-crown-6 ether, using non-anhydrous tetrahydrofuran as the solvent. The potassium hydroxide is used to produce an alkoxide ion from the alcohol while the 18-crown-6 ether acts as a phase-transfer agent. The reaction proceeds through a classic SN-2 nucleophilic substitution. A terminal Bromo group is eliminated, and a bond is formed between the oxygen of the alcohol and the carbon of the alkane. An ether is produced between the n-carbon linker and the sugar or the dye. At this stage, the terminal Bromo group that remains may react under the same conditions with the free alcohol of a corresponding sugar or dye. The condensation product is then deprotected.